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Efficient synthesis of NIR emitting bis[2-(2'-hydroxylphenyl)benzoxazole] derivative and its potential for imaging applications.
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2020-01-15 , DOI: 10.1016/j.bioorg.2020.103585
Junfeng Wang 1 , Hannah Baumann 2 , Xiaoman Bi 2 , Leah P Shriver 2 , Zhaoda Zhang 3 , Yi Pang 4
Affiliation  

Unassymetric bis[2-(2'-hydroxyphenylbenzoxole)] bis(HBO) derivatives with a DPA functionality for zinc binding have been developed with an efficient synthetic route, using the retrosynthetic analysis. Comparison of bis(HBO) derivatives with different substitution patterns allows us to verify and optimize their unique fluorescence properties. Upon binding zinc cation, bis(HBO) derivatives give a large fluorescence turn-on in both visible (λem ≈ 536 nm) and near-infrared (NIR) window (λem ≈ 746 nm). The probes are readily excitable by a 488 nm laser, making this series of compounds a suitable imaging tool for in vitro and in vivo study on a confocal microscope. The application of zinc binding-induced fluorescence turn-on is successfully demonstrated in cellular environments and thrombus imaging.

中文翻译:

NIR发射双[2-(2'-羟苯基)苯并恶唑]衍生物的高效合成及其在成像应用中的潜力。

使用逆合成分析,已经开发出具有有效的合成途径的具有DPA官能团的锌的不对称双[2-(2'-羟基苯基苯并恶唑)]双(HBO)衍生物。比较具有不同取代模式的bis(HBO)衍生物,可以验证和优化其独特的荧光性质。结合锌阳离子后,bis(HBO)衍生物在可见光(λem≈536 nm)和近红外(NIR)窗口(λem≈746 nm)中都提供大的荧光开启。探针很容易被488 nm激光激发,这使得该系列化合物成为在共聚焦显微镜上进行体外和体内研究的合适成像工具。在细胞环境和血栓成像中已成功证明了锌结合诱导的荧光开启的应用。
更新日期:2020-01-15
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